Skip to main content
SpringerLink
Log in

Water mediated one-pot synthesis and biological evaluation of 1,2,3-triazolyl-1,4-dihydropyridine hybrids

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Design and synthesis of a new series of 1,2,3-triazolyl-1,4-dihydropyridine hybrids (5a–5l) have been accomplished by a one-pot multicomponent reaction of o-propargyl salicylaldehyde/o-propargyl naphthaldehyde, β-keto compounds, ammonium acetate, and organic azides in short reaction times. In vitro antibacterial studies of the newly synthesized hybrids were investigated against four different human pathogens, viz. S. aureus, Proteus mirabilis, E. Coli, and K. Pnemonia, and the results were compared with that of the standard drug, tetracycline. Also, their anti-inflammatory activity was studied against bovine serum albumin (BSA) and compared with that of the reference drug, dichlofenac. Some of the hybrids show good antibacterial and anti-inflammatory activities comparable with that of the reference drugs.

Graphical Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. A.C. Gaudio, A. Korolkovas, Y. Takahata, J. Pharm. Sci. 83, 1110 (1994)

    Article  CAS  Google Scholar 

  2. R. Mannhold, B. Jablonka, W. Voigt, K. Schönafinger, E. Schraven, Eur. J. Med. Chem. 27, 229 (1992)

    Article  CAS  Google Scholar 

  3. G.L. Reid, P.A. Meredith, F. Pasanisi, J. Cardiovasc. Pharmacol. 7, 18 (1985)

    Article  Google Scholar 

  4. C. Safak, R. Simsek, Mini-Rev. Med. Chem. 6, 747 (2006)

    Article  CAS  Google Scholar 

  5. N. Edraki, A.R. Mehdipour, M. Khoshneviszadeh, R. Miri, Drug Discov. Today 14, 1058 (2009)

    Article  CAS  Google Scholar 

  6. X.-L. Wang, K. Wan, C.-H. Zhou, Eur. J. Med. Chem. 45, 4631 (2010)

    Article  CAS  Google Scholar 

  7. Y. Jin, H. Zhao, H. Lu, C.M. Kuemmel, J. Zhang, D. Wang, Molecules 20, 1088 (2015)

    Article  Google Scholar 

  8. Z.-J. Wang, Y. Gao, Y.-L. Hou, C. Zhang, S.-J. Yu, Q. Bian, Z.-M. Li, W.-G. Zhao, Eur. J. Med. Chem. 86, 87 (2014)

    Article  CAS  Google Scholar 

  9. A. San-Féalix, R. Alvarez, S. Veláazquez, E. De Clercq, J. Balzarini, M.J. Camarasa, Nucl. Nucleotides 14, 595 (1995)

    Article  Google Scholar 

  10. F. Reck, F. Zhou, M. Girardot, G. Kern, C.J. Eyermann, N.J. Hales, R.R. Ramsay, M.B. Gravestock, J. Med. Chem. 48, 499 (2005)

    Article  CAS  Google Scholar 

  11. S. Nagarajan, P. Shanmugavelan, M. Sathishkumar, R. Selvi, A. Ponnuswamy, H. Hariharan, V. Shanmugaiah, Chin. Chem. Lett. 25, 419 (2014)

    Article  CAS  Google Scholar 

  12. S. Nagarajan, M. Sathishkumar, P. Shanmugavelan, R. Ranganathan, A. Ponnuswamy, R. Venkatesan, V. Shanmugaiah, Eur. J. Med. Chem. 58, 464 (2012)

    Article  CAS  Google Scholar 

  13. R.M. Kumbhare, U.B. Kosurkar, P.K. Bagul, A. Kanwal, K. Appalanaidu, T.L. Dadmal, S.K. Banerjee, Bioorg. Med. Chem. 22, 5824 (2014)

    Article  CAS  Google Scholar 

  14. R. Marco-Contelles, R. León, C. de los Rios, A. Guglietta, J. Terencio, G.M. López, A.C. Garcia, M. Villarroya, J. Med. Chem. 49, 7607 (2006)

    Article  CAS  Google Scholar 

  15. K.V. Sashidhara, M. Kumar, V. Khedgikar, P. Kushwaha, R.K. Modukuri, A. Kumar, J. Gautam, D. Singh, B. Sridhar, R. Trivedi, J. Med. Chem. 56, 109 (2013)

    Article  CAS  Google Scholar 

  16. A. Hantzsch, Justus Liebigs Annalen der Chemie. 215, 1 (1882)

    Article  Google Scholar 

  17. L.M. Wang, J. Sheng, L. Zhang, J.W. Han, Z. Fan, H. Tian, C.T. Qian, Tetrahedron 61, 1539 (2005)

    Article  CAS  Google Scholar 

  18. R. Surasani, D. Kalita, A.V.D. Rao, K. Yarbagi, K.B. Chandrasekhar, J. Fluor. Chem. 135, 91 (2012)

    Article  CAS  Google Scholar 

  19. M.M. Heravi, K. Bakhtiri, N.M. Javadi, F.F. Bamoharram, M. Saeedi, A. Oskooie, J. Mol. Catal. A: Chem. 264, 50 (2007)

    Article  CAS  Google Scholar 

  20. S.R. Cherkupally, R. Mekalan, Chem. Pharm. Bull. 56, 1002 (2008)

    Article  CAS  Google Scholar 

  21. M. Maheswara, V. Siddaiah, G.L.V. Damu, C.V. Rao, Arkivoc. 2, 201 (2006)

    Google Scholar 

  22. A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 50, 5248 (2009)

    Article  CAS  Google Scholar 

  23. J. Safari, S.H. Banitaba, S.D. Khalili, J. Mol. Catal. A: Chem. 335, 46 (2011)

    Article  CAS  Google Scholar 

  24. N.N. Karade, V.H. Budhewar, S.V. Shinde, W.N. Jadhav, Lett. Org. Chem. 4, 16 (2007)

    Article  CAS  Google Scholar 

  25. K. Aswin, K. Logaiya, P.N. Sudhan, S.S. Mansoor, J. Taibah Univ. Sci. 6, 1 (2012)

    Article  Google Scholar 

  26. J.G. Colle, R.S. Miles, B. Watt, T.J. Mackie, J.E. McCartney, Practical Medical Microbiology, fourteenth edn. (Churchill Livingstone, Edinburg, 1996)

    Google Scholar 

  27. L. Essers, K. Radebold, Clin. J. Microbiol. 12, 641 (1980)

    CAS  Google Scholar 

  28. P.A. Villanova, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically, Approved standard NCCLS publication M7-A3, 3rd edn. (NCCLS, Villanova, 1993)

    Google Scholar 

  29. R. Sribalan, M. Kirubavathi, G. Banuppriya, V. Padmini, Bioorg. Med. Chem. Lett. 25, 4282 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank IRHPA, DST for providing the 300 MHz NMR instrument for recording the NMR spectra of the compounds synthesized and UGC-BSR for giving financial support.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, Tamilnadu, 625 021, India

    Sivasubramaniyan Archana, Murugan Dinesh, Raja Ranganathan & Alagusundaram Ponnuswamy

  2. Offshore Platform and Marine Electrochemistry Centre, CSIR - CECRI Unit, V.O.Chidambaranar Port, Tuticorin, 628 004, India

    Patchaiah Kalaiselvi, Subbiah Chellammal & Gopalan Subramanian

  3. Department of Physics, Thanthai Periyar Government Institute of Technology, Vellore, Tamilnadu, 608 002, India

    Saminathan Murugavel

Authors
  1. Sivasubramaniyan Archana
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Murugan Dinesh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Raja Ranganathan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Alagusundaram Ponnuswamy
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Patchaiah Kalaiselvi
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Subbiah Chellammal
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Gopalan Subramanian
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Saminathan Murugavel
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alagusundaram Ponnuswamy.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1082 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Archana, S., Dinesh, M., Ranganathan, R. et al. Water mediated one-pot synthesis and biological evaluation of 1,2,3-triazolyl-1,4-dihydropyridine hybrids. Res Chem Intermed 43, 187–202 (2017). https://doi.org/10.1007/s11164-016-2614-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2614-8

Keywords

Search

Navigation